18-Crown-6 → n-Octyl fluoroformate

HRID 64989Notes

Reaction equation

HRID 64989 reaction equation
[C:1](=[O:15])(OC(Cl)C)[O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[F-:16].[K+].C1OCCOCCOCCOCCOCCOC1>>[F:16][C:1]([O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[O:15]

Participants

4

Reactant 3

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 13506636Octyl 1-chloroethyl carbonate

Product 1

HCID 11286774n-Octyl fluoroformateYield 86%

Conditions

Temperature
85 °C

Procedure

A mixture of 10.6 g (0.045 mole) of previously distilled octyl 1-chloroethyl carbonate, 4.5 g (0.08 mole) of dry KF and 0.6 g (0.002 mole) of 18-crown-6 ether is stirred and warmed at about 85° C. (oil bath ) under a pressure of about 1.87 kPa. After 12 hrs., all the volatile acetaldehyde has evaporated. The mixture is cooled and distilled under reduced pressure. There is obtained 6.87 g of pure n-octyl fluoroformate (86%). b.p.: 74°-77° C. at 533 Pa (4 mmHg).

Workup

  1. custom, all the volatile acetaldehyde has evaporated
  2. temperatureThe mixture is cooled
  3. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-7a829267d23b4134993e464ff2060310
Source dataset
uspto-grants-1986_09
Patent number
US04612143

Reaction notes

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